Stereocontrolled synthesis of (+)-boronolide

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3513-3516

  Trost, Barry M ^a   Yeh, Vince S C ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONOLIDE; LACTONE;

AFRICAN MEDICINE; ARTICLE; CHEMISTRY; MEDICINAL PLANT; PLANT; STEREOISOMERISM; SYNTHESIS;

LACTONES; MEDICINE, AFRICAN TRADITIONAL; PLANT COMPONENTS; PLANTS, MEDICINAL; STEREOISOMERISM;

EID: 0037015434     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026665i     Document Type: Article

References (42)

1. Recent reviews of polyol natural product synthesis, see: (a)-Rychnovsky, S. D. Chem. Rev. 1995, 95, 2012.
2. (b) Schneider, C. Angew. Chem., Int. Ed. 1998, 37, 1375. See also: Enders, D.; Ince, S. J.; Bonnekessel, M.; Runsink, I.; Raabe, G. Synlett 2002, 962.
3. (b) Schneider, C. Angew. Chem., Int. Ed. 1998, 37, 1375. See also: Enders, D.; Ince, S. J.; Bonnekessel, M.; Runsink, I.; Raabe, G. Synlett 2002, 962.
4. For reviews on asymmetric aldol bond constructions using chiral enolates, see: (a) Evans, D. A. Asymmetric Synth. 1984, 3, 2.
5. (b) Heathcock, C. H. Asymmetric Synth. 1984, 3, 111.
6. (c) Heathcock, C. H.; Kim, B. M.; Williams, S. F.; Masamune, S.; Paterson, I.; Gennari, C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford 1991; Vol. 2.
7. (c) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317.
8. For reviews on catalytic enantioselective aldol reactions, see: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
9. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer; Heidelberg, 1999; Vol. 3. p 998.
10. (c) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: 2000; p 493.
11. (d) Carreira, E. M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: 2000; p 513.
12. Aldol reactions: (a) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003.
13. (b) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
14. (c) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. Nitro aldol reactions:
15. (d) Trost, B. M.; Yen, V. S. C. Angew. Chem., Int. Ed. Engl. 2002, 41, 861.
16. (e) Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett, 2002, in press.
17. For the catalytic asymmetric synthesis of syn- or anti-diols by binol type catalysts, see: (a) Yoshikawa, N.; Suzuki, T.; Shibasaki, M. J. Org. Chem. 2002, 67, 2556.
18. (b) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2466. For synthesis of anti-diols by proline: Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
19. (b) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2466. For synthesis of anti-diols by proline: Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
20. (a) Franca, N. C.; Polonsky, J. C. R. Acad. Sci. Paris 1971, 273, 439.
21. (b) Davis-Coleman, M. T.; Rivett, D. E. Phytochemistry 1987, 26, 3047.
22. Watt, J. M.; Brandwijk, M. G. B. The Medicinal and Poisonous Plants of Southern and Eastern Africa; Livingston: Edinburgh, 1962; p 516.
23. (a) Van Puyvelde, L.; Dube, S.; Uwimana, E.; Uwera, C.; Domisse, R. A.; Esmans, E. L.; Van Schoor, O.; Vlietinck, A. Phytochemistry 1979, 18, 1215.
24. (b) Van Puyverde, L.; De Kimpe, N.; Dube, S.; Chagnon-Dube, M.; Boily, F.; Borremans, F.; Schamp, M. J. O. Phytochemistry 1981, 20, 2753.
25. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003. First recemic synthesis, see: Jefford, C. W.; Moulin, M.-C. Helv. Chim. Acta 1991, 74, 336.
26. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003. First recemic synthesis, see: Jefford, C. W.; Moulin, M.-C. Helv. Chim. Acta 1991, 74, 336.
27. Nagano, H.; Yasui, H. Chem. Lett. 1992, 1045.
28. Honda, T.; Horiuchi, S.; Misutani, H.; Kanai, K. J. Org, Chem. 1996, 61, 4944.
29. Examples of L-selectride reduction of ketones via Felkin-Anh model: (a) Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc. 1988, 110, 4685.
30. (b) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 3769.
31. (c) Faucher, A.; Brochu, C.; Landry, S. R.; Duchesne, I.; Hantos, S.; Roy, A.; Myles, A.; Legault, C. Tetrahedron Lett. 1998, 39, 8425.
32. (a) Carlsen, P. H.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
33. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. J. Org. Chem. 1997, 62, 5497.
34. Keck, G.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265.
35. Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. R.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962.
36. Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
37. (a) Racherla, U.; Brown, H. C. J. Org. Chem. 1991, 56, 401.
38. (b) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570.
39. For recent reviews on RMC, see: (a) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
40. (b) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013.
41. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
42. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S.L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.